


Bye Baby

by TheLittleRedWhoCouldWrite



Category: Supernatural
Genre: Alternate Universe - Human, Alternate Universe- Criminal, Background Sabriel, Criminal Dean, Criminal Gabriel, Dead John Winchester, Destiel - Freeform, Established Gabriel/Sam Winchester, Implied Sexual Content, M/M, Openly Bisexual Dean
Language: English
Status: In-Progress
Published: 2015-10-13
Updated: 2016-03-22
Packaged: 2018-04-26 07:11:55
Rating: Mature
Warnings: Graphic Depictions Of Violence, Major Character Death
Chapters: 12
Words: 8,623
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4995079
Author URL: https://archiveofourown.org/users/TheLittleRedWhoCouldWrite/pseuds/TheLittleRedWhoCouldWrite
Summary: <blockquote class="userstuff">
              <p>Castiel Novak wants nothing more than to be an actor. His life takes a very different turn when he meets bad boy Dean Winchester.</p>
            </blockquote>





	1. November 2, 1983

**Author's Note:**

> Cover edited by me.  
> Can also be found on  
> Wattpad: http://w.tt/1La123Q  
> The SPN Amino app: http://aminoapps.com/p/lek9v  
> And hopefully soon Tumblr as well.
> 
> Please leave comments. As this is only my second fanfiction, I would absolutely love to hear what you guys think.

** **

**Pontiac , Illinois**

"Castiel Novak, it's your mother's funeral!"

The dark-haired eight year old pulls his pillow over his head. "No, it's not!"

Jimmy Novak sighs and sits on the edge of his son's bed. "Castiel..."

"I don't want to go."

"Son-"

"Leave me alone!"

"Come on."

Castiel doesn't fight his father as he is led across the street to the churchyard. There's already a small gathering of people. They part easily to let the pair through. Jimmy keeps a firm arm around Castiel's shoulders. The preacher begins speaking, but Castiel isn't listening. He's staring at the closed casket and marble headstone.

_In Loving Memory of Amelia Novak_

_Beloved Mother, Wife, and Friend_

_April 3, 1953-October 23, 1983_

Suddenly, the small boy jerks away from his father and bolts. He runs down the street, through some yard, and into the back lot of the movie theater. He slumps against a wall and cries.

XXXXXX

**Lawrence, Kansas**

"You'll never catch me!" four-year-old Dean Winchester proclaims, toy car gripped tight in one small fist as he runs from his mother.

Mary laughs and scoops her son up. "Gotcha!"

Dean wriggles, dropping his toy and giggling. Then he settles against her. "Go see Sammy now?" he asks.

"Of course." She carries him upstairs and into the nursery. "Go say goodnight to your brother." She sets him down in the doorway and he runs to his brother's crib.

Dean leans over the side to kiss his brother's forehead. "'Night, Sam."

Smiling, Mary leans over to kiss her youngest son as well. "Good night, love."

"Hey, Dean."

Dean turns and runs to the man in the doorway. "Daddy!"

"Hey, buddy" John says, scooping him up. "Whaddaya think, you think Sammy's ready to toss around a football?"

"No, Daddy!"

"No," John chuckles.

"You got him?" Mary asks, passing them in the doorway.

"I got him," he assures her, hugging Dean closer. He looks to the crib. "Sweet dreams, Sammy." He flips off the lights and carries Dean out.


	2. January 5, 2014

**On a back road outside Pontiac, Illinois**

"Whoo! Listen to her purr," Dean proclaims, AC/DC's "Back in Black" pouring from the stereo. "Have you ever heard anything so sweet?"

Sam stared incredulously at his brother. "If you two want to get a room, just let me know."

Dean runs a hand over the dashboard. "Don't listen to him, Baby, he doesn't understand. 'Sides, it's not like he and the dentist's wet dream in the back seat have any room to talk."

"I'll have you know I've never had a cavity in my life," Gabriel announces around his sucker.

If I find wrappers back there, I swear-"

"Yeah, yeah, Dean-o," Gabe interrupts. "I hear ya."

Dean shoots him a skeptical look in the rearview mirror. "How far to Pontiac?"

Sam checks the GPS on his phone. "'Bout three hundred miles."

"Good."

He lays on the gas.

XXXXXX

"Damn it!"

Castiel kicks the front tire of his car- the one he pulled over to change, only to have his car refuse to start. He then flops down against it, head on his hands. Today is not going his way.

The wail of an electric guitar reaches him, accompanied by the roar of an engine. Castiel's head shoots up and in the distance he sees the sun off the roof of a car. He leaps to his feet, waving his discarded shirt over his head.

The car, a sleek black older model he can't identify, comes to a stop beside him. The passenger window rolls down, but the occupants of the vehicle are cast into shadow.

"You need help?" a deep voice that sends shivers down his spine asks.

"Your assistance would be very much appreciated, yes," Castiel responds.

The car pulls over to park in front of Castiel's beat-up 1978 Lincoln Continental Mark V. The engine turns off and from the driver's side emerges the most attractive man Castiel has ever laid eyes on.

He's tall- a few inches over Castiel's six foot- with a strong jaw and dark blonde hair, cut short. Plump pink lips curl into a smile under bright green eyes. Castiel can't help following the line of his body down strong arms, a t-shirt clad torso, and muscular bowed legs wrapped in worn jeans.

Castiel is suddenly very aware of his own shirtless state.

"Well, hello, there," the stranger says, eyes raking over Castiel as a small smirk graces his lips.

"Hello," Castiel stammers as the doors on the passenger side of the car open and two more men get out.

One is a giant, broad-shouldered and muscular, with long brown hair touching just under his jaw and fox-tilted eyes of an indiscernible color. Despite his size, the man appears to be very gentle, if the way he looks at and touches the other man is any indication. The final man is small and only looks smaller next to the giant. He has blonde hair, a slightly hawkish nose, and mischievous eyes Castiel can only describe as sunlight through whiskey.

The beautiful green-eyed man is approaching, eyeing the open hood of Castiel's car. "What seems to be the problem."

"I haven't the faintest idea," Castiel responds.

The man is bending over the car, a focused look on his face. "Sammy, get the jumper cables from the trunk, will ya?" he says after a few minutes. "There's a whole lot more wrong than the battery, but a jump should at least get you to a garage." He trades the keys for the cables the giant- Sam- brings. "Turn Baby 'round for me."

"Sure thing," Sam replies.

The green-eyed man straightens up, wiping his hands on a cloth he pulls from his back pocket. He holds out a hand to Castiel. "Dean Winchester."

"Castiel Novak," Castiel responds, shaking the offered hand. "Thank you for assisting me. I'm afraid my knowledge of cars is rather limited."

"I figured," Dean says, shooting him a wink. "This poor car needs some love." Sam has parked Dean's car so it's nose-to-nose with Castiel's, but not touching. "That's my little brother, Sam," Dean tells Castiel. He jerks his hand to the third man. "That's Gabriel, Sammy's husband."

"Hiya," Gabriel says, waving.

"What're you doing out here anyways?" Dean asks as he hooks the jumper cables to his own car.

"I'm returning from Chicago," Castiel informs him.

"Chicago, huh? What's in Chicago?"

They wait a minute. Castiel tries the car, but it doesn't start. "An audition," he says finally, in answer to Dean's question.

That seems to get Dean's attention. "An audition? What for?"

"An independent film. I did not get the role."

"What? That's ridiculous."

"Excuse me?"

"I mean, look at you. You're made for movies. Those eyes and that just-got-laid hair..." he trails off, eyeing Castiel and licking his lips. That one move has Castiel's slack's tightening.

Castiel blushes and smooths his hair self-consciously. "I do not typically appear this disheveled."

"Well, you should. It's a good look on you. Try it again."

He does. The car starts. Dean whoops and Sam rolls his eyes.

"Where're you headed?" Dean asks, slamming the hoods of both cars and tossing the cables to Sam.

"Pontiac," Castiel answers, sliding into his driver's seat.

"Same here. I'm going to follow you, make sure you get to a garage. That okay?" he leans against Castiel's door.

"Yes, Dean, that's fine."

The man grins cheekily and straightens up. "We'd better get going. 'S getting late. Lead the way, buddy."

The remainder of the drive to Pontiac is uneventful. Castiel heads to his preferred garage, a little establishment a mere block from his apartment.

"Thank you again, Dean," he says to the man, who's leaning against his own car.

Dean waves him off. "Happy to help."

"If I have the available room, I would offer my apartment for you tonight, but it lacks sufficient space."

"That's fine," Dean says, straightening up. "We're tough. We'll be in town a few weeks. Who knows, maybe we'll see each other again, Cas."

"Cas?"

"Castiel is a mouthful." Dean seems a little sheepish. "I hope you don't mind."

Castiel smiles. "I do not mind." He leans in and plants a small kiss to the side of Dean's mouth. "As a token of my gratitude. Goodnight, Dean."

He turns to start the walk home. He makes it a mere twenty feet before he hears, "Hey, Cas!" He turns to see dean hurrying to catch up.

"Yes, Dean?" he says when the man reaches him.

Dean pulls Castiel to him and kisses him firmly. Castiel smiles, hands coming up to grip the front of Dean's shirt as he returns it.

They reluctantly break apart when Gabriel starts cat-calling. Blue eyes meet lust-blown green. A smirk passes over plump pink lips.

"Here's looking at you, kid," Dean murmurs with a wink before he pulls away and returns to his car, leaving a dazed Castiel to stare after him.


	3. January 7, 2014

"Good luck," Cas tells Mrs. Morgan, handing her the lottery ticket she just bought. She totters away and Cas- he enjoys the sound of the nickname- throws her receipt in the trash under the counter as the next customer approaches. He straightens up, taking not of the six-pack of beer that is been placed beside the register. "Is this- Dean!"

Green eyes sparkle mischievously. "Hiya, Cas," Dean says, setting beef jerky and Mentos beside the beer. "This is it for me."

Cas starts ringing him up. "I was not expecting to run into you so soon."

"I've been looking for you," Dean responds. "What are you doing tonight?"

"Nothing, why?"

"See, there's this gorgeous man with these stunning blue eyes that I would really like to take one a date."

Cas blushes. How can Dean make him blush so easily? "A date?"

"A date. This is kind of a first for me, but whaddaya say? I'll pick you up at six?"

Cas nods as Dean hands him his debit card. "I would like that very much." He grabs a pen and scrawls his phone number and address on the back of Dean's receipt. "I'll be waiting."

XXXXXX

Cas is hard pressed to make it through the rest of that day. Meg, a childhood friend, comes in at one point to do nothing more than blatantly flirt with him. He does his best to deflect her efforts and she leaves in a huff. He feels bad about it, but he is not, nor will he ever be, interested in her. She just doesn't seem to understand that.

Six finds him frantically checking himself over in the bathroom mirror for the hundredth time. He's dressed in a pale blue button-up and jeans, and is trying to muss his hair just so when there's a sharp knock at the door.

Dean is dressed in dark jeans, clean boots, and a green dress shirt that makes his eyes pop.

"Hey," he says, rubbing the back of his neck. "Ready?"

Cas nods and Dean smiles. He leads the way downstairs to where his sleek black car is parked.

"I'm afraid I'm not familiar with this model of car," Cas admits as Dean runs a loving hand over the roof.

"This here's my Baby," Dean says. Cas gets the feeling "Baby" is capitalized. Something in Dean's voice makes it sound like a title. "She's a 1967 Chevy Impala. She was my dad's, but not she's mine."

"She's beautiful," Cas tells him, sliding into the passenger seat. "You must take very good care of her."

"She takes good care of me," Dean says fondly. 'I'm just returning the favor."

The Impala rumbles to life, the sound alone enough to send warm tingles south. The car is an extension of her driver and it has an effect on Cas.

"Where are we going?" he asks, studying the man beside him.

"Dinner at a diner I stumbled across the other night, and then I figured we could just drive for a while. Maybe talk. I hope you don't mind. I don't really know the area well enough."

"That's fine with me, Dean."

"Good. I've got blankets and beer in the trunk is we ever feel like parking somewhere, so we're set."

XXXXXX

Cas is an interesting date. His strange way of talking is amusing, his smile is contagious, and his blue eyes are mesmerizing.

Dinner is great. The conversation flows, the food is good- turns out Cas loves burgers, too; can he get any more perfect?- and the pie is delicious. All too soon, he finds himself pulling off the side of a backroad at Cas' request.

"Grab the beer, will ya?" he says, pulling blankets from the trunk.

They lay one out on the hood. Cas is already shivering, so Dean tucks the smaller man up against his side and covers them both with the extra blankets.

"Better?" he asks, leaning them both back against the windshield.

"Yes, Dean," Cas says. "Thank you."

Cas is looking at the stars, but Dean only has eyes for the blue-eyed man. Shit, he's getting sappy in his old age.

"You're not looking at the stars," Cas points out. After all, that's why he'd asked Dean to pull over in the first place.

"What does Castiel mean?" Dean blurts out.

Cas smiles, laying his head against Dean's shoulder. Dean Winchester does not get butterflies. Okay, maybe he does. _Damnit, Cas, what are you doing to me?_

"Castiel is the Angel of Thursday," he explains. " My mother wished to name me after an angel and I was born on a Thursday. Does Dean mean anything specific?"

"I was named after my grandma, Deanna, who died before I was born." Why is he telling Cas this? "Sam was named after her husband, Samuel."

"Your mother's parents?"

"Yeah."

"What is your mother like?"

A lump forms in Dean's throat. "She was beautiful and kind and I..." he trails off.

"She's dead."

Dean nods. "My dad, too."

"I'm sorry."

"I don't remember much- I was four, Sammy was barely six months. Dad only lasted a year before he put a bullet in his own head. My Uncle Bobby raised us."

Cas reaches over to slide his fingers through Dean's. for some reason, Dean doesn't pull away. "If it is any consolation, my mother is dead, as well."

Dean looks down at the man, who has lifted his head so he can look Dean in the eye.

"I like you, Cas," Dean finds himself admitting.

A soft blush spread across Cas' cheeks. "I like you, too, Dean."

After that, it's no problem at all to lean down and press their lips together. Cas' hand immediately comes up to grip the back of Dean's head. The kiss quickly becomes heated. Cas releases the blankets so he can straddle Dean's lap. Dean's hands scrabble at the buttons of the other man's shirt.

Suddenly, Cas shivers. "Too cold," he murmurs against Dean's mouth.

"Car?" Dean suggests breathlessly.

Cas grins. "Car."


	4. January 8, 2014

Dean locks the Impala and stretches, grinning to himself. He just dropped Cas off at his apartment. It's about two in the morning now, but he doesn't mind.

The lights are off in the room he's sharing with Sam and Gabe, and there's no "Do Not Disturb" sign on the door, but he still knocks before going inside.

"Y'all are decent?" he asks.

"Yes, Dean," Sam says. "Enjoy your date?"

Dean locks the door and flops down on his designated bed. Sam and Gabe are cuddled together in the other bed. Sam is clearly trying to sleep, but Gabe is doing something on his husband's laptop.

"Three words," Dean says. "Cas does yoga."

Sam groans and Gabe chuckles. "Way to go," the smaller man says. "While you were getting laid, I was casing out next job."

"Gabe-" Sam starts.

"Talk to me," Dean interrupts.

"The dollar store down the road. One room, money kept in a safe under the counter. There's two cameras- one above the door, one in a corner. I've already hacked the feeds, so I know the combo for the safe." Sam huffs and turns his back to Gabe, who adds, "It's only a two man job, Samsquatch. I'll go in and Dean-o'll keep watch. We don't even need to take the Impala. It'll be simple."

"I don't like it," Sam grumbles.

"When do you think we should go?" Dean asks, pulling his black pants and shirt from his duffle.

"They open at eight. We'd have six hours if we went now."

"More than enough time. Let's do this."

XXXXXX

Famous last words.

Dean grunts as the cop shoves him over the hood of a cruiser. Gabe hits the hood next to him.

"Well, this didn't go as planned," Gabe says.

"Sam is going to kill you."

"How was I supposed to know about the alarm?"

"You said you cased the joint!"

"Shut up," a cop snaps. "Put them in separate cruisers."

Gabe wiggles his eyebrows at Dean before he's pulled away.

XXXXXX

Cas hunches over in the booth, hands wrapped around his cup of coffee. He's pleasantly sore, but dead tired, and has work in a half hour.

"Hey, handsome," Meg coos, sliding into the bench beside him. "Rough night?"

"Yes," he responds, not deigning to look at her. "If you mean rough in the good way."

"Diane told me about your date last night. You can do better, Castiel. After all, Roy brought your date in around three this morning with another guy. They got caught robbing the dollar store on the edge of town."

Cas' stomach twists. Dean? Arrested? "Excuse me, I'm going to be late for work."

Hot coffee spills over his fingers as he practically shoves his way past her. When he makes it to his car, he locks the door behind him and pulls out his cell phone. He scrolls through his contacts to the first of two Dean put in before dropping Cas off this morning.

"This is Dean. If I didn't give you this number, go away. If I did, leave a message and I'll call you when I can."

Cas feels sick. He quickly scrolls to the second contact.

"Hello?" the voice is tired and laced with unhappiness.

"Is this Sam?"

"Yeah."

"Sam, this is Castiel. Dean isn't answering his phone."

There's a small pause, and then, "Dean and Gabe were arrested this morning."

So Meg was telling the truth and not just trying to manipulate Cas. "What for?"

"They were robbing the dollar store by our motel. I told them it was a bad idea, but they never listen. Look, Cas- can I call you Cas?"

"Yes."

"Cas, this isn't anything new. Those two have been getting in trouble since their early teens. They don't play well with the law. It would be in your best interest to just forget about Dean."

"Sam. I've seen how you interact with Gabe. I know you understand that I can't do that."

Sam sighs. "Yeah, I do understand. Can you come over?"

"I have work, but I get off at five-thirty."

"Come to the Palamar Motel as soon as you get off. Room 113. Hopefully I'll have more news by then."

XXXXXX

The Palamar Motel is a disgusting establishment. Cas reluctantly parks beside the Impala and knocks at Room 113.

Sam looks exhausted. His eyes are red from crying, not something Cas expected from Sam. It just proves what a soft heart Sam really has.

"Hey, Cas," he says, holding the door open to let Cas in.

"Any word?" Cas asks.

"Yes, they've already set a date- the thirteenth. I think I can get you in to visit Dean, but I'm not sure. It took a lot of persuading to be able to visit Gabe." The big man sits on the edge of the bed furthest from the door. He looks impossible small for someone so large. "I hate when this happens. They always manage to get out early on good behavior, but that doesn't make it any easier."

"I'm sure it doesn't," Cas says, feel a pang of sympathy. After all, while he may be falling for Dean already, Sam and Gabe have been together at least a decade, possibly longer. This is Sam's husband. "Have you eaten at all today, Sam?"

He shrugs. "I think I ate a granola bar this morning."

Cas nods. "Stay here. I'm going to go get food. Is there anything you are absolutely opposed to eating?"

"McDonalds," Sam says, making a face. "Or anything Dean would probably eat. Salads are usually safe. But you don't have to do this."

"Nonsense. I'm going. I'll be back in a half hour."


	5. January 13, 2014

Cas is on edge for the next few days. He can't go to the trial because of his work schedule, but Sam has promised to give him all the details afterwards. Which is why he's pacing in the younger man's motel room, wringing his hands. Finally, the rumble of the Impala's engine can be heard outside. Cas practically runs to the door when Sam opens it.

"Well?" he asks.

Sam looks even worse since Cas saw him when the boys were first arrested. He runs a tired hand through his hair, leaning back against the door.

"They've both got two years," he says. "With early release on good behavior. Dean'll be out in a few days, no doubt about it, and he's going to bring Gabe with him, but Cas..." the big man lifts his head. "I don't want that. I never wanted any of this, I just..." he trails off with a choked sound, sliding to the floor and pulling his knees to his chest.

Cas is curious, but senses Sam needs a moment to calm down. He kneels beside his new friend and lays a steady hand on his shoulder, waiting patiently.

"Gabe and I started dating when I was sixteen," Sam finally says. "We've known each other our whole lives, so it was a natural progression of sorts. It was on and off for a while, but we always came back together. We broke it off when I went to Stanford, to study law- I would've stayed there, too, if Gabe hadn't showed up at my apartment. I don't know why I went with him, but I did." He lifts his head to meet Cas' eyes. "I love him, Cas, but I want a normal life! I've been emailing back and forth with counselors at Stanford. They're willing to give me back my place, full-ride included. But Gabe can't stay out of trouble. He just doesn't..."

Sam lets out a soft sob, scrambles to his feet, and vanishes into the bathroom. The door locks behind him.

Cas moves to the bed as the shower turns on. Two years. He can't see Dean handling that well. The man is reckless to a fault and brutally honest on occasion. He's going to get himself in trouble- more trouble than he already has.

XXXXXX

Dean's not sure how they manage to get transferred the same day as the trial, but it happens. These guys are really desperate to not have to deal with Dean and Gabe any more. It probably doesn't help that Gabe can't keep his mouth shut. So Dean's not too surprised to find himself being led to his new home for the next two years.

His cell mate, a big man with hair longer than Sam's and a beard, immediately claims the top bunk. Dean turns to see Gabe shooting him a desperate look from the cell across the hall.

Prison, turns out, isn't really as bad as people make it sound. So long as you keep your head down and your nose clean, both of which are things Dean has problems with. Doesn't help that he's so good looking- Pretty, as several inmates have already nicknamed him. Everyone wants a taste.

Dean is far from helpless. Fifteen minutes into lunch, he's already been put in a headlock by a guard.

"You calm?" the guard snarls.

"Yeah, I'm calm," Dean says.

The guard releases him and he straightens up, twisting his neck and rubbing it. The barrel of a gun is suddenly shoved under his chin, pushing it up a little.

"What's your name?" the guard asks, eyes narrowed.

"Winchester," Dean responds, keeping as much snark and attitude out of his voice as he can.

"Well, Winchester, consider this your first warning. Three warnings gets you into solitary overnight. I don't pull punches. So watch your step."

Dean manages a small nod and the gun is pulled away. He swallows hard and returns to his table. No one bothers him for the rest of lunch.


	6. January 18, 2015

**Palamer Motel, Pontiac, Illinois**

Sam listens patiently to the man on the other end of the phone.

"Yes, officer," he says. "If I see him, you'll be the first to know."

For the first time in his life, he means it.

XXXXXX

**Castiel's apartment, Pontiac, Illinois**

Cas' brow furrows in confusion and his eyes pop open. He glances at the clock- 4:27 AM. Who could be knocking on his door at this time of day?

He rolls out of bed with a groan, trying to tie his robe before finally giving up and letting it hang open. He stumbles to the door.

He's barely managed to open it before Dean is shoving his way in. Cas jumps back, suddenly wide awake.

"Dean?" he cries.

"Shhh," Dean hisses, locking the door and gazing through the peephole. "Okay, we're good." He turns to a stunned Cas with a smarmy grin on his face. "Hey, baby."

"But... I... how...?" Cas stammers.

Dean silences him with a fierce kiss. "I've missed that," he admits, sliding his hands along Cas' waist under the robe. "I like this look on you."

Cas can feel exactly how much Dean likes it pressed firm against his hip. "Dean-"

"Broke out. The details don't matter. I need you, Cas." The last bit is said in a growl that send the blood rushing south.

"Bedroom's this way," he responds.

XXXXXX

**Palamar Motel, Pontiac, Illinois**

Sam knows who's at the door without having to check.

"Gabe," he sighs, yanking the smaller man into the room. "You are going to be the death of both of us some day."

"Missed ya, too, Samsquatch," Gabe chuckles, stretching up on his toes for a kiss.

Sam pulls away, holding his phone up. "I've got the deputy on speed dial. We're going to have a nice long talk."

Gabe is suddenly serious. "Police? What are you doing? Have you done crazy?"

"No," Sam replies. "Quite the opposite. I've finally come to my senses. You, Gabriel, are going back to jail."

"Going back?! Why would I do that? Sam, I just got out. C'mere, obviously you missed me so much you're delusional."

"This isn't a joke, Gabe. I mean it. I love you, but this isn't the life I want for us. I want to go back to Stanford, get my degree. Gabe, I want a normal life for us, and if it means you have to go back to jail first, so be it. I'm putting my foot down on this."

Gabe is stunned. "Sammy, you don't understand."

"I know it sucks. I get that. But, Gabe, listen. I want us to live long happy lives together, but that ain't gonna happen is you keep going the way you are."

The shorter man walks around Sam to sit on the end of their bed. He's usually silent for a long time, staring down at his hands in his lap. Finally, he looks up into his husband's eyes.

Do I have to turn myself in right now?" he asks, abnormally quiet.

Sam grins, setting his phone on the nightstand. "Of course not. it's 4:30 in the morning. We've got time."

Gabe immediately brightens up. "C'mere, then, big guy."

XXXXXX

**Castiel's apartment, Pontiac, Illinois**

"So, Gabe is free as well?" Cas asks, trailing his fingertips down the center of Dean's chest.

The two are tangled- Dean refuses to use cuddled- together in Cas' bed. Cas has the day off and they're making use of it.

"Yep," Dean answers. "He and Sammy are probably making good use of the alone time."

Cas makes a thoughtful sound, adjusting his head on Dean's chest. "Round two?" he inquires.

"Hell, yes."

XXXXXX

**Palamar Motel, Pontiac, Illinois**

Sam collapses beside Gabe with a groan. He husband turns to grin lazily at him.

"We've still got it," he remarks.

Sam laughs softly and pulls him in for a kiss. A sharp knock at the door interrupts them.

"You two better get decent fast!" Dean shouts.

Sam sighs and Gabe laughs. They clean up quickly and throw on whatever clothes they can reach. Gabe ends up with Sam's shirt over his boxers, so Sam settles for going shirtless.

He's just zipped up his jeans when Dean bursts in, Cas right behind him.

"Don't say I never got you nothin'," Dean tells Sam, smirking at the couple.

"Yeah, about that," Sam says. "Gabe, isn't there something you want to tell Dean?" he shoots his husband a pointed look.

Gabe looks nervous. "I... I'm... I'mturningmyselfin."

Dean stares. "What?"

"I'm turning myself in," Gabe repeats. It's clear he's having a hard time getting the words out. "Sam and I talked it over. We both have things we want to do with our lives." He's gaining confidence now. "Things we can't do living the way we are. So, I'm going to do my time and then Sam's going back to Stanford. There's nothing you can do to change my mind."

Dean is stunned, but Cas steps forward to lay his hand on Gabe's shoulder. "Alright," he says firmly before letting his hand drop. He turns to Dean. "Sam and I are going to get breakfast."

"We are?"

"Yes, Sam."

XXXXXX

Dean barely registers Cas and Sam leaving.

"Sam talked you into this," he finally says. It's not a question.

"Sam brought it up. I made my own decision."

Dean scoffs. "You can't lie to me, Gabe. He flashed you the puppy eyes and you caved. I know how you two work."

"Doesn't matter, Dean-o. I've made up my mind." Gabe digs in his duffle and pulls out a candy bar. "I'm sure going to miss these."

"I guess I'll have to make sure Sam always has some to sneak in to you."


	7. January 19, 2014

**Palamar Motel, Pontiac, Illinois**

Sam wakes slowly, warm and comfortable. Gabe is tucked neatly against him, sunlight through the curtains making his hair glow.

Sam smiles down at his husband and peppers Gabe's face with soft kisses. The smaller man hums, stirring. Whiskey gold eyes flutter open and a smirk crosses his lips.

"Mornin', Sammy," he purrs, running his hand over Sam's abs.

"Mornin'," Sam replies, rolling to cover Gabriel with his body while trailing kisses down his neck. He sucks a hickey on his soft throat, where every inmate will see it and know Gabe is his.

XXXXXX

"Best way to wake up," Gabriel proclaims, throwing the soiled towel aside. He crawls back onto the bed. "How're you doin', big guy?"

Sam's eyes are said. It breaks Gabe's heart to see the love of his life like this.

"I wish you didn't have to go," Sam says.

Gabe pulls the big man to him, pressing kisses to Sam's forehead. "I wish I didn't have to go, too. but just think of all the sex we'll have to make up for when I get out."

Sam laughs softly. "I'm not letting you out of bed for the first week."

"Attaboy. I'm looking forward to it."

Sam clings to Gabe a while before rolling out of bed to put on clothes. Gabe reluctantly follows suit. They cuddle together on the couch and Sam calls the sheriff before he loses his nerve.

When he hangs up, he pulls Gabe into his lap and hides his face in his husband's neck. They just sit there, holding each other until the knock at the door breaks them apart.

Gabe kisses Sam softly before getting up to open it. "Morning, officers," he says, lacking the energy to be a smart mouth. "I suppose you're here to arrest me."

While the officers cuff Gabe and read him his rights, he has eyes for only Sam.

"Still love me?" he asks.

Sam nods, eyes shiny.

"Good. I love you, too."

XXXXXX

**Just outside of Pontiac, Illinois**

'A-ramble on, and now's the time, the time is now.

Sing my song, I'm goin' 'round the world.

I've gotta find my girl.

On my way,I've been this way ten years to the day.

I gotta ramble on, I gotta find the queen of all my dreams,

I tell you no lie.'

Dean hums along to the song, head bobbing. The countryside flies by. He's about fifteen minutes from Pontiac and he can't wait to get back.

He's never felt like this. Sure, he's had his fair share of one night stands. He is Dean Winchester, after all. But nothing like this. He's never dated. He's never had butterflies in his stomach. He's never felt like he could fly at just the thought of his lover.

He's so screwed, but he can't bring himself to care.

He pulls Cas' car into the parking lot of the apartment building. Cas' usual spot is located around the side, hidden by big trees.

Dean grabs the two duffels from the trunk and heads upstairs. He already has a key, so he just lets himself in. that's something else that's new. He's never had a key to someone's place before.

"Honey, I'm home!" he calls cheerfully.

Cas is in the kitchen, stirring something in a big pot on the stovetop. "There you are," he says. "Just in time. Dinner's almost ready."

It's all very domestic. Dean's not sure what to think of it, but he drops the duffels on the couch and joins Cas in the tiny kitchen. "Smells good," he says, slipping his arms around the dark-haired man's waist and and pressing a kiss behind his ear.

"I promise, it will taste just as good. Now, wash up and set the table."

"Yes, sir."

"Sam's joining us, so set three places."

"Sam?"

"Yes, Sam. He should not be alone tonight, so I invited him over." Cas pulls a long, foil-wrapped something from the oven. "You will be considerate. Sam needs our support right now."

"Alright, Cas." If it were anyone else, Dean might've protested. He wants to, but he's already learned there's no point. Cas has made up his mind on this.

Dinner is white chicken fettuccini alfredo, with a salad and French bread- buttered, sprinkled with garlic, and toasted in the over- on the side. Cas doesn't like any form of alcohol, so they have water to drink.

Sam is quiet, but Dean keeps the conversation going. He jokes a little, sensing Sam needs it. His brother insists on helping with clean-up. As soon as the dishes are done, he drops the Impala keys on the counter and excuses himself. Cas offers to drive him back to the motel, but Sam assures him he's fine walking and leaves.

"That went well," Cas says once Sam's gone. "Oh, that reminds me. How did the job go?"

"Went off without a hitch," Dean says, sitting on the couch and moving the duffel bags to the floor. "Oh, and I brought you something." He digs around in one of the bags a moment before pulling out a tan bundle of cloth. He shakes it out, revealing it to be a long tan trench coat with a belt around the waist.

"Oh," Cas says, reaching for it. "Oh, Dean."

"It's probably a little big, but I though it suited you. If you don't like it, I can-"

"Don't like it? Dean, it's perfect!" Cas pulls on the coat. It's a little big on his lean runner's frame, but he doesn't seem to mind. Instead, he straddles Dean's lap and kisses him soundly. "Thank you."

Dean chuckles, smoothing the coat on his lover's shoulders. "Well, then, I guess I'm going to have to bring you things more often."

Cas smirks. "But first, you should help me take this off."

"Hmm, happily."


	8. February 14, 2014

**Castiel's apartment, Pontiac, Illinois**

Cas wakes to an empty bed.

He frowns, sitting up. The other side has definitely been slept in, but is now cold. Dean has been gone a while.

"Dean?" he calls, getting out of bed. He snatches up his robe and wraps it around himself as he steps out into the main area of the apartment.

No Dean.

There are on impala keys in the bowl on the counter and no beat-up boots by the door. Cas rushes back to the bedroom and throws open the closet door. Dean's duffels are gone as well.

It feels like he's been stabbed in the heart. He sits heavily on the bed, trying to comprehend. Everything was going well. Cas knows Dean is a drifter at heart, but he thought the green-eyed man was happy.

He tries calling, but it just goes straight to voicemail. Sam is no help, either- he hasn't spoken to Dean for a few days- but he agrees. It had seemed like Dean was happy with Cas.

Cas gets ready for work in a daze. He eats a breakfast of cold cereal and coffee. As soon as he gets to work, everyone picks up on his mod. They tiptoe around him all morning, shooting each other worried glances. Cas notices. He's heartbroken, not blind.

Lunch rolls around. Cas heads to the café next door and isolates himself in a corner booth. He tries Dean's number again.

"This is Dean Winchester-"

Cas hangs up and calls Sam.

"Hey, Cas."

"Sam, have you heard from Dean?"

"No, nothing yet. He'll call me soon and you'll be the first to know when he does. Promise."

Cas nods, slumping in his seat. "Thank you, Sam."

"No problem, Cas."

After hanging up, Cas sets the phone on the table in front of him and rubs his hands over his face.

"Trouble in paradise?" an all too familiar voice says smugly.

"Leave me alone, Meg," he says.

She's already pressing herself against his side. "What, bad boy get bored?"

"I've already told you, I have not seen Dean."

"And I've already told you I know you're lying. You're lucky I like you. Otherwise, you would be in big trouble."

"Go away."

"Why should I?"

Cas really isn't in the mood for this. "Because right now, I really hate you. Go. Away."

Meg is stunned into silence- a definite first. Slowly, she draws back, and then Cas hears her footsteps departing.

He forces himself through the rest of the day, wanting nothing more than to go home.

Finally- finally- the end of the say arrives. He takes the long way home, though, suddenly unwilling to return to an empty apartment.

He has to eventually, though. He slowly makes his way up three flights of stairs to find the front door unlocked.

Cas frowns. He knows he locked it when he left this morning. The only people with keys are his father and...

Dean.

His heart beats faster as he kicks off his shoes and tosses his vest onto the couch. He throws open the bedroom door, more than ready to give his lover a stern talking to, and stops dead in his tracks.

"Hiya, Cas," Dean says with a smile, hands behind his head. "Happy Valentine's Day."

Cas is speechless. He slowly takes in the candles on the nightstand, the red silk sheets, and Dean's lean golden body spread out on the mattress, dressed only in...

"Dean," he chokes out. "Are those... panties?"

"Yep, silk and lace," the man replies, rolling onto all fours and wiggling his hips at Cas. "What do you think?"

Cas is more than happy to show Dean exactly what he thinks. He reinforces it three days later when he gifts Dean with a box containing six more pairs in various colors and fabrics. Dean thanks him by modeling them and the white lace pair look so damn innocent in comparison to the man's mischievous green eyes that Cas just can't help himself.


	9. February 22, 2014

**A convenience store in Pontiac, Illinois**

Dean's grin is wild. He's on an adrenaline high and he loves it.

"Pick up the pace," he snaps, waving his gun in a way that makes the man behind the counter flinch.

The man shoves the rest of the money in the bag and pushes it across the counter. Dean zips it up and tosses the bag over his shoulder.

"Thank you very much," he says, snatching a pack of beef jerky on his way out.

He tosses the bag in the trunk of the impala, stuffing jerky in his mouth. He tucks his gun in his thigh holster.

XXXXXX

  
**Jimmy Novak's house, Pontiac, Illinois**

"I don't like the sound of this boy."

Cas sighs. "Father, Dean is a fine young man."

"An arrest warrant does not constitute a fine young man. Castiel, think of your future. No one will ever hire you is you have an arrest record."

"I'm not doing anything wrong!"

"Except harboring a criminal."

XXXXXX

"Put your hands in the air."

Dean's gun is in his hand and he whirls to find three guns pointing at him. Pouting, he lifts his hands.

"You boys always spoil my fun," he grumbles, glaring at the cops.

"Finger off the trigger," the far right cop says, as if Dean had never spoken.

He obeys.

"Put the gun on the ground."

Dean reluctantly sets his beloved Colt down.

"Step away from the weapon."

He rolls his eyes, but does as he's told.

The cop jerks his head at his companions. "Cuff him."

XXXXXX

"I'm just saying, get out while you still can. If you turn Dean in now, they'll probably go easier on you."

"Father, this discussion is over. I have to get home. I want to have dinner ready when Dean gets back."

Cas doesn't wait for his father's reply, but he makes sure to slam the door behind him. He takes the shortest route back to his apartment. Part of him is disappointed to find that Dean's not back yet, but part of him is relieved. He has a pie to make.

He's up to his elbows in flour when the phone rings, naturally. He uses a towel to protect it as he picks it up and hits the answer button.

"Hello?" he says, balancing the phone between his ear and his shoulder as he pours filling into the pie crust.

"Cas, it's Sam."

"Hello, Sam. You sound rather flustered. Is something wrong?"

"Dean's been arrested again."


	10. March 8, 2014

**Pontiac Correctional Center, Pontiac, Illinois**

Sixteen years.

Cas can still hear the judge, even as he pulls into the parking lot of the Pontiac Correctional Center a week later.

"Castiel Novak, here to see Dean Winchester," he tells the guard at the visitor's desk.

The guard types something on his computer, and then nudges the man next to him. "Take Mr. Novak down to visiting."

The man grumbles, but leads Cas down several hallways to the visiting room. He selects he first booth and tries to be patient.

Wearing a bright orange jumpsuit, Dean looks like death warmed over. Cas' heart clenches at the sight of his bruised cheekbone and black eye. Despite his injuries, Dean visibly brightens when he sees who's waiting for him.

He yanks the phone off the cradle. "Cas," he breathes, laying a hand against the glass. "Cas."

"Hello, Dean," Cas says with a small smile, lining his fingers up with his lover's. "I apologize for not visiting sooner. My father has been rather bothersome."

"Doesn't matter," Dean says, voice rough. "I've missed you so much."

"I've missed you, too. Dean, what happened to your face?"

The green-eyed man shakes his head. "It's not important."

"Dean-"

"One of the inmates harbors a certain amount of hatred for me- no clue why. But don't worry, babe, I can handle it."

Cas bites his lip. "I understand you are more than capable, but that does not stop me from worrying."

Dean smiles fondly. "I know. I'll be fine, darlin'. Have my things been given to Sam?"

"Yes."

"Do you think you could bring some things in for me?"

"What things?"

"My pictures of you and my family."

Cas nods. "Of course, Dean. I'll bring them in a few days."

"Thanks," Dean says with a smile.

"Time's up," the guard on Cas' side grunts.

He doesn't want to go. "Good-bye, Dean," he says quietly.

'Bye, Cas."

Cas drives home in silence. When he reaches his apartment, he strips down to his boxers, throws on Dean's AC/DC t-shirt, and curls up in his bed. Silent tears wet his pillow.


	11. Match 12, 2014

**Pontiac Correctional Center, Pontiac, Illinois**

Dean's overjoyed when Cas brings in the pictures. He tucks them inside his jumpsuit, close to his heart.

"I miss you," Cas says, clutching the envelope Dean gave him.

"Miss you, too," Dean replies. "I'll be out before you know it you just gotta be patient, sweetheart."

"You will stay on the right side of the law once you're out, correct?"

"'Course, Cas." Dean's not sure he can keep that promise.

Cas nods. "Alright." The guards both call for time's up. "Bye, baby." The words are strange to hear from Cas, but Dean can't help a smile.

"See ya, sugar."

XXXXXX

**A few miles from the Pontiac Correctional Center, Pontiac, Illinois**

Cas taps his fingers nervously on the wheel of the Impala. He's followed the instructions in Dean's letter to the "t." There are four duffels in the trunk, as well as anything else Cas deemed necessary. He's placed a large amount of money in his savings, which is split between several banks. All that's missing is Dean.

He glances at the clock- 12:22, three minutes since he last checked. Dean should be here soon.

Finally, he sees a figure running along the dusty backroad. He squints, considering the way the person is moving, but the night makes it difficult.

The figure reaches the car and knocks on the hood- "Shave and a Haircut," like had agreed upon.

Cas lets out a sigh of relief and gets out of the car. Dean is still dressed in his orange jumpsuit, though he's now wearing a blue jacket over it. Neither serve as much protection from the cold, as evidenced by his shivering.

"Dean," Cas murmurs, pressing warm lips to cold ones. "Come on, get in. You're freezing."

They get into the backseat, where Dean awkwardly changes into warm, dry clothes. It's difficult in the cramped space, but he succeeds. Cas holds the man close, sharing body heat.

"We have to get going," Dean says after a few minutes. "They weren't far behind. You got the map?"

"Yes, Dean."

"You're wonderful." Dean kisses him. "Now, let's get out of here."


	12. March 13, 2014

**Sioux Falls, South Dakota**

They reach Sioux Falls around nine in the morning, having driven almost non-stop since leaving Pontiac. Cas drove the first half so Dean could sleep a little and warm up. Now, Cas is curled up with his head pillowed by Dean's thigh, sound asleep.

Dean glances down for the hundredth time and smiles fondly. Cas' hair is a little messy, partially because he's asleep and partially because Dean can't keep his hands out of it. He hates to wake the sleeping man, but they'll be at Bobby's soon.

"Cas," he murmurs, rubbing his right hand down Cas' arm.

Cas mumbles sleepily, stirring. Hazy eyes blink open.

"There you are," Dean says. "Time to wake up. We're almost to Bobby's place."

His lover grumbles, but sits up. He rubs his eyes sleepily and stretches the best he can.

"Sleep well?"

Cas glares and Dean chuckles.

"We can nap at Bobby's. Plus, the man makes excellent coffee."

"He better."

Dean chuckles, stopping at a corner. "C'mere, baby." He pulls Cas across the seat and kisses him, almost tenderly. "You're adorable."

That just makes Cas pout more. "'m not adorable. I'm very manly," he protests, arms folded over his chest.

"Whatever you say," Dean assures him, kissing him again.

It's not much further to Bobby's place. Rumsfield goes nuts as soon as the Impala's tires hit the gravel drive. By the time Dean's parked and gotten out of the car, a grizzled older man in a baseball cap is standing on the front porch.

"Hiya, Bobby," Dean calls, helping Cas get the bags from the trunk.

"If you bring cops to my house, so help me boy-" the man says.

"It'll be fine. Good to see you, too."

Bobby rolls his eyes and pulls Dean into a rough hug. "Damn idjit. 'Least you had the sense to call ahead this time." He eyes Cas, who is still looking rather rumpled between the trench coat and sleep-mussed hair. "This your man?"

Cas shifts the bag he's holding in order to free a hand, which he holds out for Bobby to shake. "Castiel Novak, sir."

"Pleasure. Get inside, I made coffee."

Dean leads Cas upstairs to the guest room they'll be sharing. They dump the bags on the floor by the bed and head back down to the kitchen.

"Where's Sam?" Bobby asks, leaning against the counter to nurse his mug of coffee. The younger men have settled on water, since they're planning on napping. "Figured he woulda come with ya."

"Nah, he stayed in Pontiac," Dean replies. "He persuaded Gabe to serve his time and is going to stick around till he's out. Then they're gonna head back to Palo Alto."

"Well, I'll be. Boy's been wanting to get his husband back on track for year. Glad he finally did it."

"Yes, well, I'm down a partner."

That gets Cas attention. "Dean, you promised-"

"Not now, sweetheart. This is a conversation for after our nap." How could I forget what I promised Cas? I'm screwed for real now. Dean offers Cas his hand. "C'mon, let's go rest up. we'll be in better condition to have this talk with a couple more hours of sleep under our belts."

Cas reluctantly follows Dean back upstairs. They strip down to their boxers, curl up together under the sheets, and are out within minutes.

XXXXXX

Cas wakes first. He hums softly, pushing his nose into Dean's chest and taking a deep breath of the man's familiar scent. He wants nothing more than to cuddle closer and fall back asleep, but he can't get what Dean said before their nap out of his head.

He wriggles free of Dean's arms and sits up, turning to place his feet on the floor. Cas rubs his hands over his face.

"Cas?"

He doesn't move.

Calloused hands slide over his bare back and the bed shifts as Dean moves closer. "Cas, babe, look at me."

Cas doesn't look.

"Darlin', you can't just ask me to stop. It's the only life I know."

"You promised," Cas says softly.

"I know."

"Dean, I want to get to Hollywood. I want to be famous. I can't do that is I'm helping you on the side."

"Hey, hey, I'm not asking you to. Look, a couple of jobs should get enough dough to get to Hollywood. We'll get you a fancy, well-known agent and you'll be famous in no time. I can see it, babe. You, on the red carpet in a tailor-made suit. They'll love you."

Cas finally turns, eyes shining. "Really?" he says hopefully.

"Really," Dean says firmly. "Just wait. You'll be making headlines in no time. Now, c'mere. Lunch isn't for an hour and I've yet to thank you properly."

"For what?"

"Being awesome. For being the best boyfriend ever."

Cas lights up. "Boyfriend?"

"Shut up and let me kiss you."


End file.
